title: Fluorinated substrates result in variable leakage of a reaction intermediate during catalysis by dehydroquinate synthase.
abstract: Incubation of (3S)-3-fluoro-3-deoxy-D-arabino-heptulosonate 7-phosphate with dehydroquinate (DHQ) synthase from three phylogenetically distinct sources resulted in the production of (6S)-6-fluoroDHQ and its epimer 1-epi-(6S)-6-fluoroDHQ. The differences in the product ratios of the reactions catalysed by each enzyme imply that 1-epi-(6S)-6-fluoroDHQ formation occurs by an unusual partial leakage of a reaction intermediate from the enzyme.
authors.affiliation: Institute of Fundamental Sciences, Massey University, Private Bag, 11222, Palmerston North, New Zealand.
authors.forename: Leonardo
authors.initials: L
authors.lastname: Negron
authors.forename: Emily J
authors.initials: EJ
authors.lastname: Parker
mesh_terms: D001233:Aspergillus nidulans / Q000201:enzymology*; D055162:Biocatalysis; D004926:Escherichia coli / Q000201:enzymology*; D017611:Fluorine Compounds / Q000737:chemistry* / Q000378:metabolism; D007536:Isomerism; D015394:Molecular Structure; D019761:Phosphorus-Oxygen Lyases / Q000378:metabolism*; D020027:Pyrococcus furiosus / Q000201:enzymology*; D013379:Substrate Specificity
chemical_list: D017611:Fluorine Compounds; D019761:Phosphorus-Oxygen Lyases